US2876075A - Fluorine fluorosulfonate and process for producing same - Google Patents
Fluorine fluorosulfonate and process for producing same Download PDFInfo
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- US2876075A US2876075A US587920A US58792056A US2876075A US 2876075 A US2876075 A US 2876075A US 587920 A US587920 A US 587920A US 58792056 A US58792056 A US 58792056A US 2876075 A US2876075 A US 2876075A
- Authority
- US
- United States
- Prior art keywords
- fluorine
- fluorosulfonate
- sulfur trioxide
- producing same
- reactor
- Prior art date
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- MDNHCPNENWHUHH-UHFFFAOYSA-N sulfurofluoridic acid;hydrofluoride Chemical compound F.OS(F)(=O)=O MDNHCPNENWHUHH-UHFFFAOYSA-N 0.000 title claims description 23
- 238000000034 method Methods 0.000 title claims description 13
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 26
- 229910052731 fluorine Inorganic materials 0.000 claims description 19
- 239000011737 fluorine Substances 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 239000007789 gas Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229910052802 copper Inorganic materials 0.000 description 6
- 239000010949 copper Substances 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- KWVVTSALYXIJSS-UHFFFAOYSA-L silver(ii) fluoride Chemical compound [F-].[F-].[Ag+2] KWVVTSALYXIJSS-UHFFFAOYSA-L 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- -1 compounds thionyl fluoride Chemical class 0.000 description 3
- UQSQSQZYBQSBJZ-UHFFFAOYSA-M fluorosulfonate Chemical compound [O-]S(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-M 0.000 description 3
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical group FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000005935 Sulfuryl fluoride Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 2
- LSJNBGSOIVSBBR-UHFFFAOYSA-N thionyl fluoride Chemical compound FS(F)=O LSJNBGSOIVSBBR-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 241000695274 Processa Species 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 239000012042 active reagent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000012025 fluorinating agent Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 230000002070 germicidal effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- VMUWIFNDNXXSQA-UHFFFAOYSA-N hypofluorite Chemical compound F[O-] VMUWIFNDNXXSQA-UHFFFAOYSA-N 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- 229940006461 iodide ion Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229940096017 silver fluoride Drugs 0.000 description 1
- REYHXKZHIMGNSE-UHFFFAOYSA-M silver monofluoride Chemical compound [F-].[Ag+] REYHXKZHIMGNSE-UHFFFAOYSA-M 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- DUGWRBKBGKTKOX-UHFFFAOYSA-N tetrafluoro(oxo)-$l^{6}-sulfane Chemical compound FS(F)(F)(F)=O DUGWRBKBGKTKOX-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B17/00—Sulfur; Compounds thereof
- C01B17/45—Compounds containing sulfur and halogen, with or without oxygen
- C01B17/4561—Compounds containing sulfur, halogen and oxygen only
Definitions
- a second object of the invention is to provide an-effective method for preparing the above compound.
- fluorine fluorosulfonate is the most powerful oxidizing agent, being capable of forming oxygen by reacting with an aqueous solution of sodium hydroxide. It is more easily liquefied than the others, with the exception of thionyl fluoride. It can be safely handled as a liquid at room temperature under moderate pressure. In general thionyl fluoride, the other compound of equally low volatility, acts as a reducing agent rather than an oxidizing agent. Fuorine fluorosulfonate is of potential value as an oxidant for fuels in rocket propulsion.
- fluorine fluorosulfonate contains an hypofluorite group (O-F), known to be highly toxic, and since its hydrolysis also gives rise to hydrofluoric acid, it follows that fluorine fluorosulfonate may be used as a poisonous gas for germicidal, insecticidal or other purpose. Because of its convenient liquid range and its stability, it may be more safely handled than any other known hypofluorite. Most of the known hypofluorites are explosive.
- Fuorine fluorosulfonate is also useful as a chemical reagent for producing other compounds. It can behave either as a fluorinating agent or as a reagent which introduces fluorosulfonate groups into molecules. For example, it has been found to combine with sulfur trioxide to form a substance of the formula S O F which appears to have the structure O OSOOSO F F In general the hypofluorites are active reagents. Because of its stability and relative ease of handling, fluorine fluorosulfonate should be more useful than most of the others.
- Fluorine fluorosulfonate may be prepared by causing sulfur trioxide vapor to react with fluorine at a tempera- 2,876,075 en e Mer- 3 ICC diameter of three inches and a length of three feet. This s was packed with ten pounds of copper ribbon of 0.018 inch width and .002 inch thickness. The ribbon was uniformly plated with silver having a total weight of one fourth pound. This ribbon was packed as a tangled mass into the reactorand it filled the reactor from end to end. The ends were then closed by copper plates fastened tightly in place with silver solder. Three copper tubes of A inch diameter. to be used as inlets or outlet for .gas streams were attached to the reactor.
- the product was fractionally distilled in conventional laboratory apparatus.
- sulfuryl fluoride was found to be present in the distillate.
- tion vessel is required to produce fluorine fluorosulfonate nor that the reaction of sulfur trioxide with fluorine occurs only in the presence of a mass of copper ribbon coated with silver fluoride. It is necessary, however, that 'the temperature of the reaction vessel be well above that of the room. Temperatures of 175 C. to 280 C. are known to be satisfactory.
- the gas reacts at roomrtemperature with a solution.
- fluorine fluorosulfonate SO F 1 i 2.
- a process of producing fluorine fluorosulfonate which comprises contacting fluorine and sulfur trioxide at temperatures in excess of 3.
- a process as defined in claim 2 in which the fluorine is used in excess of the amount consumed by reacting with sulfur trioxide.
- a process of producing fluorine fluorosulfonate which comprises contacting fluorine and sulfur trioxide at temperatures within the range 200 C. to 230 C.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
United States Patent George 'Cady, Seattle, Wash., and Francis B. Dudley,
Armidale, New South Wales, Australia v No Drawing. Application May 29, 1956 Serial No. 587,920
9 Claims. c1. 23-203) A second object of the invention is to provide an-effective method for preparing the above compound.
It has heretofore been known that the elements fluorine, oxygen and sulfur are found combined together in the compounds thionyl fluoride (S01 2), thionyl tetrafluoride (SOF and sulfuryl fluoride (SO F but the compound, fluorine fluorosulfonate, has not been known.
Boiling points of these substances are respectively: S OF --30 C.; SOF -48 C.; .SO F 52 C.; SO F -31.3 C. Of these, fluorine fluorosulfonate is the most powerful oxidizing agent, being capable of forming oxygen by reacting with an aqueous solution of sodium hydroxide. It is more easily liquefied than the others, with the exception of thionyl fluoride. It can be safely handled as a liquid at room temperature under moderate pressure. In general thionyl fluoride, the other compound of equally low volatility, acts as a reducing agent rather than an oxidizing agent. Fuorine fluorosulfonate is of potential value as an oxidant for fuels in rocket propulsion. Since fluorine fluorosulfonate contains an hypofluorite group (O-F), known to be highly toxic, and since its hydrolysis also gives rise to hydrofluoric acid, it follows that fluorine fluorosulfonate may be used as a poisonous gas for germicidal, insecticidal or other purpose. Because of its convenient liquid range and its stability, it may be more safely handled than any other known hypofluorite. Most of the known hypofluorites are explosive.
Fuorine fluorosulfonate is also useful as a chemical reagent for producing other compounds. It can behave either as a fluorinating agent or as a reagent which introduces fluorosulfonate groups into molecules. For example, it has been found to combine with sulfur trioxide to form a substance of the formula S O F which appears to have the structure O OSOOSO F F In general the hypofluorites are active reagents. Because of its stability and relative ease of handling, fluorine fluorosulfonate should be more useful than most of the others.
Properties of fluorine fluorosulfonate and its method of preparation are disclosed in a paper by the inventors and their research colleague, David F. Eggers, Jr., in the Journal of the American Chemical Society, vol. 78, pp. 290-292 (1956).
Fluorine fluorosulfonate may be prepared by causing sulfur trioxide vapor to react with fluorine at a tempera- 2,876,075 en e Mer- 3 ICC diameter of three inches and a length of three feet. This s was packed with ten pounds of copper ribbon of 0.018 inch width and .002 inch thickness. The ribbon was uniformly plated with silver having a total weight of one fourth pound. This ribbon was packed as a tangled mass into the reactorand it filled the reactor from end to end. The ends were then closed by copper plates fastened tightly in place with silver solder. Three copper tubes of A inch diameter. to be used as inlets or outlet for .gas streams were attached to the reactor. Two of these were inlet tubes located near one end of the reactor and on diametrically opposite sides of the cylinder. The outlet tube was attached at the opposite end of the reactor from the inlets. The temperature of the vessel was controlled by regulating the flow of electricity through two caused to enter one inlet and a stream of sulfur trioxide vapor diluted by nitrogen was caused to enter the other inlet. Both streams flowed simultaneously and the reactor was held at a temperature between 200 C. and 230 C. The flow rates of fluorine and nitrogen were regulated by valves on cylinders containing the gases. One of the nitrogen streams flowed at a rate of 5 liters per hour and was passed over a mass of the solid polymer of sulfur trioxide at room temperature. In this way the nitrogen became mixed with sulfur trioxide vapor and this mixed gas entered one inlet of the reactor. The other nitrogen streamv flowed at an average rate of 3 liters per hour and to it fluorine was added. This mixture entered the second inlet of the reactor. As the product gases left the reactor they were passed through a glass trap cooled externally by liquid oxygen. Crude fluorine fluorosulfonate condensed in the trap, but nitrogen and unreacted fluorine passed through. The presence of fluorine in the gas flowing from the trap could be detected by its odor or by its reaction with potassium iodide solution. Paper moistened with potassium iodide solution was used for the test. When this paper was held in the stream of gas emerging from the trap, it turned brown (due to free iodine), if fluorine were present. In operating the system, care was taken to pass fluorine at a rate high enough to constantly have fluorine emerging from the condenser trap. This meant that an excess of fluorine over that required for reaction with sulfur trioxide was present in the reactor.
To refine the crude fluorine fluorosulfonate obtained in this way, the product was fractionally distilled in conventional laboratory apparatus. In addition to fluorine fluorosulfonate, sulfuryl fluoride was found to be present in the distillate.
In one run using the above procedure 13.8 grams of sullfur trioxide was caused to react. From this an 8.4 gram quantity of refined fluorine fluorosulfonate was obtained.
It has also been found possible to produce fluorine fluorosulfonate by passing fluorine over sulfamic acid held in a nickel tube at 200 C.
On the basis of work done by the inventors there is neither reason to feel that any particular form of reac- 'parture from the spirit of the invention tion vessel is required to produce fluorine fluorosulfonate nor that the reaction of sulfur trioxide with fluorine occurs only in the presence of a mass of copper ribbon coated with silver fluoride. It is necessary, however, that 'the temperature of the reaction vessel be well above that of the room. Temperatures of 175 C. to 280 C. are known to be satisfactory.
The compound, fluorine fluorosulfonate, has been recognized as a new substance by analysis and by its properties. Eight measured values for the vapor density ranged from 117.0 to 119.5 with an average of 118.6 grams per 'gram molecular volue. (Theoretical for SO F is 118.0); Analyses gave the values: sulfur 26.1,
I 27.03, 26.6, 26.4%' by Weight; fluorine 31.5, 31.3, 32.0,
The gas reacts at roomrtemperature with a solution.
of sodium hydroxide liberating oxygen and leaving in solution fluoride and fluorosulfonate ions. It reacts with a solution containing iodide ion and forms free iodine.
Although only certain forms of the invention have been described, those skilled in the art will recognize that numerous modifications may be made in the procedure for preparing fluorine fluorosulfonate without dea or the scope of the appended claims. 7
What we claim is:
1. As a new chemical compound, fluorine fluorosulfonate (SO F 1 i 2. A process of producing fluorine fluorosulfonate which comprises contacting fluorine and sulfur trioxide at temperatures in excess of 3. A process as defined in claim 2 in which the fluorine is used in excess of the amount consumed by reacting with sulfur trioxide.
4. A process as defined in claim 2 in which the vapors from the reaction are cooled to a temperature below 31 C. to condense fluorine fluorosulfonate.
5. A process as defined in claim 4 in which the condensed product is refined by fractional distillation, thereby giving fluorine fluorosulfonate of high quality.
6. A process as defined in claim'2 in which the reactants are mixed with an inert gaseous diluent.
7. A process of producing fluorine fluorosulfonate which comprises contacting fluorine and sulfur trioxide at temperatures Within the range 200 C. to 230 C.
8. A processas defined in claim 2 in'which the gases are contacted in a reaction vessel containing a porous mass of finely divided copper coated with silver difluoride.
9. A process in which streams of fluorine and sulfur trioxide, each diluted with nitrogen, the fluorine being used in excess of the amount consumed by reaction with sulfur trioxide, are mixed in a vessel containing a porous mass of finely divided copper coated with silver difluoride at a temperature within the range 200 C. to 230 C., and the reaction product is cooled to 31 C. or below to obtain a crude condensate which is refined by fractional distillation yielding the compound fluorine fluorosulfonate.
' No references cited.
Claims (2)
1. AS A NEW CHEMICAL COMPOUND, FLUORINE FLUOROSULFONATE (SO3F2).
2. A PROCESS OF PRODUCING FLUORINE FLUOROSULFONATE WHICH COMPRISES CONTACTING FLUORINE AND SULFUR TRIOXIDE AT TEMPERATURE IN EXCESS OF 150*.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US587920A US2876075A (en) | 1956-05-29 | 1956-05-29 | Fluorine fluorosulfonate and process for producing same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US587920A US2876075A (en) | 1956-05-29 | 1956-05-29 | Fluorine fluorosulfonate and process for producing same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2876075A true US2876075A (en) | 1959-03-03 |
Family
ID=24351719
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US587920A Expired - Lifetime US2876075A (en) | 1956-05-29 | 1956-05-29 | Fluorine fluorosulfonate and process for producing same |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2876075A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3017240A (en) * | 1958-12-19 | 1962-01-16 | Du Pont | Linear inorganic polymers and process of preparing the same |
-
1956
- 1956-05-29 US US587920A patent/US2876075A/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3017240A (en) * | 1958-12-19 | 1962-01-16 | Du Pont | Linear inorganic polymers and process of preparing the same |
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